US4260551AExpiredUtility

Polyprenyl derivatives

75
Assignee: SANKYO COPriority: Nov 18, 1975Filed: Feb 12, 1979Granted: Apr 7, 1981
Est. expiryNov 18, 1995(expired)· nominal 20-yr term from priority
Inventors:Hiroshi MishimaAkira OgisoShinsaku Kobayashi
C07C 69/18C07C 45/68C07C 69/76C07C 69/16C07C 69/28C07C 69/007C07C 69/78C07C 69/56C07C 69/618
75
PatentIndex Score
10
Cited by
2
References
32
Claims

Abstract

Polyprenyl derivatives having the formula ##STR1## in which R 1 and R 2 may be the same or different and each represents hydrogen atom, hydroxyl group, an alkoxy group having 1-8 carbon atoms, an aliphatic acyloxy group having 2-18 carbon atoms, an aromatic acyloxy group or an araliphatic acyloxy group having 2-3 carbon atoms in the aliphatic acyl moiety, R 3 represents hydrogen atom, an alkyl group having 1-8 carbon atoms, an aliphatic acyl group having 2-18 carbon atoms, an aromatic acyl group or an araliphatic acyl group having 2-3 carbon atoms in the aliphatic acyl moiety, n is an integer of 1-4 and, when n is an integer of 2-4, R 2 's may be the same or different; provided that, when n is 1 or 2, at least one of R 1 and R 2 's is hydroxyl group, an alkoxy group, an aliphatic acyloxy group, an aromatic acyloxy group or an araliphatic acyloxy group. These derivatives are useful as medicines for treating peptic ulcer.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. An ester having the formula ##STR20## wherein R 1  and R 2  may be the same or different and each is selected from the group consisting of hydrogen; hydroxyl; C 1  -C 4  alkoxy; C 2  -C 12  aliphatic acyloxy; benzoyloxy; benzoyloxy substituted with C 1  -C 3  alkyl, C 1  -C 3  alkoxy or halogen; phenylacetoxy; phenylpropionyloxy; and cinnamoyloxy; R 3  is selected from the group consisting of C 2  -C 12  aliphatic acyl; benzoyl; benzoyl substituted with C 1  -C 3  alkyl, C 1  -C 3  alkoxy or halogen; phenylacetyl; phenylpropionyl; and cinnamoyl;   n is an integer of from 1 to 4, and when n is 2 to 4, the R 2  s may be the same or different; provided that at least one of R 1  and R 2  is OH, said alkoxy, said acyloxy, said benzoyloxy, phenylacetoxy, phenylpropionyloxy or cinnamoyloxy.   
     
     
       2. An ester according to claim 1 wherein R 1  represents a hydrogen atom, R 2  represents a hydrogen atom, hydroxyl, alkoxy having from 1 to 4 carbon atoms, aliphatic acyloxy having from 2 to 12 carbon atoms, benzoyloxy or cinnamoyloxy, R 3  represents an aliphatic acyl having from 2 to 12 carbon atoms, benzoyl or cinnamoyl, and n is an integer of from 1 to 3; provided that at least one of the R 2  groups is one of the specified R 2  groups other than a hydrogen atom. 
     
     
       3. An ester according to claim 1 wherein R 1  represents a hydrogen atom, the R 2  in the side chain at the 7-position of the structural formula represents hydroxyl, alkoxy having from 1 to 2 carbon atoms, aliphatic acyloxy having from 2 to 12 carbon atoms, benzoyloxy or cinnamoyloxy, R 3  represents aliphatic acyl having from 2 to 12 carbon atoms, benzoyl or cinnamoyl and n is an integer of from 1 to 3. 
     
     
       4. 7-Hydroxymethyl-3,11-dimethyl-2,6,10-dodecatrien-1-ol diacetate of the formula of claim 1. 
     
     
       5. 7-Hydroxymethyl-3,11-dimethyl-2,6,10-dodecatrien-1-ol dibenzoate of the formula of claim 1. 
     
     
       6. 7Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol diacetate of the formula, of claim 1. 
     
     
       7. 7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol dicaproate of the formula of claim 1. 
     
     
       8. 7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol dilaurate of the formula of claim 1. 
     
     
       9. 7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol dipalmitate of the formula of claim 1. 
     
     
       10. 7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol dibenzoate of the formula of claim 1. 
     
     
       11. 7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol dicrotonate of the formula of claim 1. 
     
     
       12. 7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol bis-p-methylbenzoate of the formula of claim 1. 
     
     
       13. 7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol bis-p-methoxybenzoate of the formula of claim 1. 
     
     
       14. 7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol bis-p-chlorobenzoate of the formula of claim 1. 
     
     
       15. 7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol bis-phenylacetate of the formula of claim 1. 
     
     
       16. 7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol dicinnamate of the formula of claim 1. 
     
     
       17. 11-Hydroxymethyl-3,7,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol diacetate of the formula of claim 1. 
     
     
       18. 11-Hydroxymethyl-3,7,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol dibenzoate of the formula of claim 1. 
     
     
       19. 7,15-Dihydroxymethyl-3,11-dimethyl-2,6,10,14-hexadecatetraen-1-ol triacetate of the formula of claim 1. 
     
     
       20. 7,15-Dihydroxymethyl-3,11-dimethyl-2,6,10,14-hexadecatetraen-1-ol tribenzoate of the formula of claim 1. 
     
     
       21. 7-Hydroxymethyl-3,11,15,19-tetramethyl-2,6,10,14,18-eicosapentaen-1-ol diacetate of the formula of claim 1. 
     
     
       22. 7Hydroxymethyl-3,11,15,19-tetramethyl-2,6,10,14,18-eicosapentaen-1-ol dibenzoate of the formula of claim 1. 
     
     
       23. (E,Z,E) and (E,E,E)-7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol diacetate of the formula of claim 1. 
     
     
       24. (E,Z,E) and (E,E,E)-7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol dicrotonate of the formula of claim 1. 
     
     
       25. (E,Z,E) and (E,E,E)-7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol dicaproate of the formula of claim 1. 
     
     
       26. (E,Z,E) and (E,E,E)-7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol dicinnamate of the formula of claim 1. 
     
     
       27. (E,Z,E) and (E,E,E)-7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol dibenzoate of the formula of claim 1. 
     
     
       28. (E,Z,E) and (E,E,E)-7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol dilaurate of the formula of claim 1. 
     
     
       29. (E,E,E,E), (E,Z,E,E), (E,E,Z,E) and (E,Z,Z,E)-7-Hydroxymethyl-3,11,15,19-tetramethyl-2,6,10,14,18-eicosapentaen-1-ol diacetate of the formula of claim 1. 
     
     
       30. (E,E,E,E), (E,Z,E,E), (E,E,Z,E) and (E,Z,Z,E)-7Hydroxymethyl-3,11,15,19-tetramethyl-2,6,10,14,18-eicosapentaen-1-ol dibenzoate of the formula of claim 1. 
     
     
       31. An aliphatic ester of the formula of claim 1. 
     
     
       32. An aromatic ester of the formula of claim 1.

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